Synthesis of 1,2,5,6‐/1,2,3,6‐tetrahydropyridinyl‐tetrahydro‐cyclopentaisoxazole derivatives

Abstract

Fused tetrahydrocyclopenta-isoxazoles were synthesized by 1,3-dipolar cycloaddition reactions with pyridinealdoxime or tetrahydropyridinealdoxime and cycloalkenes.

Isoxazoline, Isoxazole, and Oxadiazole Derivatives as M1 Muscarinic Acetylcholine Receptor Agonists

“…Isoxazoles 4a and 4d were also prepared by using N ‐propargyl pyrrolidinone as the dipolarophile (Scheme ). Isoxazoline 3d and isoxazole 4d with 3‐pyridyl substituent were further reacted to give tetrahydropyridine substituted compounds 3e and 4e , respectively (Scheme ).…”

“…Several nitrogen containing heterocyclic esters 5a–5f were cyclized with 1‐(2‐oxopyrrolidin‐1‐yl)acetamidoxime by the action of NaH in the presence of 4 Å molecular sieves in dry THF to yield oxadiazoles 6a–6f . Methylation and subsequent reduction of the 3‐pyridyloxadiazole compound 6d gave the tetrahydropyridyloxadiazole compound 6g (Scheme ) . 1‐(2‐oxopyrrolidin‐1‐yl)acetamidoxime could be prepared by the reaction of N ‐cyanomethylpyrrolidin‐2‐one with hydroxylamine following the known procedure …”